Structural Elucidation of the Mechanism of Molecular Recognition in Chiral Crystalline Sponges

Shi Yuan Zhang, David Fairen-Jimenez, Michael J. Zaworotko

Research output: Contribution to journalArticlepeer-review

Abstract

To gain insight into chiral recognition in porous materials we have prepared a family of fourth generation chiral metal–organic frameworks (MOFs) that have rigid frameworks and adaptable (flexible) pores. The previously reported parent material, [Co2(S-mandelate)2(4,4′-bipyridine)3](NO3)2, CMOM-1S, is a modular MOF; five new variants in which counterions (BF4, CMOM-2S) or mandelate ligands are substituted (2-Cl, CMOM-11R; 3-Cl, CMOM-21R; 4-Cl, CMOM-31R; 4-CH3, CMOM-41R) and the existing CF3SO3 variant CMOM-3S are studied herein. Fine-tuning of pore size, shape, and chemistry afforded a series of distinct host–guest binding sites with variable chiral separation properties with respect to three structural isomers of phenylpropanol. Structural analysis of the resulting crystalline sponge phases revealed that host–guest interactions, guest–guest interactions, and pore adaptability collectively determine chiral discrimination.

Original languageEnglish
Pages (from-to)17600-17606
Number of pages7
JournalAngewandte Chemie - International Edition
Volume59
Issue number40
DOIs
Publication statusPublished - 28 Sep 2020

Keywords

  • chiral binding sites
  • chiral crystalline sponge
  • chiral metal–organic frameworks
  • chiral separation and resolution
  • molecular recognition

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